script by u/worshipurdad | You and your best friend have a long-running bit where you make bets — the loser having to do what the winner wants. After you win the latest bet, his punishment is to let you pick out clothes for him while thrifting, dressing him up like a femboy. Thinking you’d be able to humiliate him with the outfits you picked out for him, you find yourself admiring him instead. The sexual tension begins to reach a high as he teases you over your flustered reaction, and you find yourself in a spot you never expected to be in as you’re forced to make eye contact with him as you jack him off.